Compositions containing isosorbide monoester and aliphatic vicinal diols

Patent metadata

Field	Value
Publication number	US-2016000080-A1
Application number	US-201214237032-A
Country	US
Kind code	A1
Filing date	Jul 31, 2012
Priority date	Aug 4, 2011
Publication date	Jan 7, 2016
Grant date	—

Abstract

What are described are compositions comprising
a) one or more compounds of the formula (I)

in which
R is a straight-chain or branched saturated alkyl group having 5 to 11 carbon atoms or a straight-chain or branched mono- or polyunsaturated alkenyl group having 5 to 11 carbon atoms, and

b) one or more aliphatic vicinal diols.

The compositions are distinguished in particular by an advantageous antimicrobial activity.

First claim

1 . A composition comprising
a) one or more compounds of the formula (I)

in which
R is a straight-chain or branched saturated alkyl group having 5 to 11, preferably 7 to 9 and particularly preferably 7 carbon atoms or a straight-chain or branched mono- or polyunsaturated alkenyl group having 5 to 11, preferably 7 to 9 and particularly preferably 7 carbon atoms, and

b) one or more aliphatic vicinal diols.

2 . The composition as claimed in claim 1 , wherein the radical R in formula (I) is a straight-chain saturated alkyl radical having 7 to 9 carbon atoms.

3 . The composition as claimed in claim 2 , wherein the radical R in formula (I) is a straight-chain saturated alkyl radical having 7 carbon atoms.

4 . The composition as claimed in one or more of claims 1 to 3 , wherein the one or more substances of component b) are selected from compounds of the formula (II)

in which
X is O, CH 2 or COO and
R is a straight-chain or branched saturated alkyl group which contains 1 to 12 carbon atoms, preferably 2 to 10 carbon atoms and particularly preferably 3 to 8 carbon atoms and in which 1 or 2 hydrogen atoms may be substituted by hydroxyl groups (OH groups) or a straight-chain or branched mono- or polyunsaturated, preferably monounsaturated, alkenyl group which contains 2 to 12 carbon atoms, preferably 2 to 10 carbon atoms and particularly preferably 3 to 8 carbon atoms and in which 1 or 2 hydrogen atoms may be substituted by hydroxyl groups (OH groups).

5 . The composition as claimed in claim 4 , wherein R in formula (II) is a non-substituted straight-chain or branched saturated alkyl group which contains 1 to 12 carbon atoms, preferably 2 to 10 carbon atoms and particularly preferably 3 to 8 carbon atoms.

6 . The composition as claimed in claim 4 or 5 , wherein the one or more substances of component b) are selected from the group consisting of 1,2-decanediol, ethylhexylglycerin, 1,2-octanediol, 1,2-hexanediol, glyceryl caprylate and glyceryl caproate.

7 . The composition as claimed in claim 6 , wherein the one or more substances of component b) are selected from the group consisting of 1,2-decanediol, ethylhexylglycerin, 1,2-octanediol and 1,2-hexanediol.

8 . The composition as claimed in claim 7 , wherein the substance of component b) is ethylhexylglycerin.

9 . The composition as claimed in one or more of claims 1 to 8 , which comprises
I) from 0.05 to 0.7, preferably from 0.1 to 0.7 and particularly preferably from 0.2 to 0.5 part by weight of isosorbide and
II) from 0.1 to 1.0, preferably from 0.2 to 1.0 and particularly preferably from 0.4 to 0.8 part by weight of isosorbide diester of the formula

where R has the meaning given for formula (I) and where the isosorbide diester is preferably isosorbide dicaprylate,

in each case based on 1.0 part by weight of the one or more compounds of the formula (I) and preferably based on 1.0 part by weight of isosorbide monocaprylate.

10 . The composition as claimed in one or more of claims 1 to 9 , which additionally comprises one or more sorbitan esters of sorbitan and carboxylic acids R a COOH, preferably selected from sorbitan esters from 1,4- and/or 1,5-sorbitan and carboxylic acids R a COOH where R a is a straight-chain or branched saturated alkyl group having 5 to 11, preferably 7 to 9 and particularly preferably 7 carbon atoms or a straight-chain or branched mono- or polyunsaturated alkenyl group having 5 to 11, preferably 7 to 9 and particularly preferably 7 carbon atoms, and the weight ratio of the one or more compounds of the formula (I) to the one or more sorbitan esters just mentioned is from 70:30 to 100:0, preferably from 80:20 to 100:0, particularly preferably from 90:10 to 100:0 and especially preferably from 95:5 to 100:0.

11 . The composition as claimed in claim 10 , wherein the one or more sorbitan esters of sorbitan and carboxylic acids R a COOH are selected from sorbitan esters of sorbitan and caprylic acid and are preferably selected from sorbitan esters of 1,4- and/or 1,5-sorbitan and caprylic acid and the sorbitan ester is particularly preferably sorbitan monocaprylate.

12 . The composition as claimed in one or more of claims 1 to 11 , which comprises, in addition to the one or more compounds of the formula (I), one or more compounds selected from the group consisting of sorbitol, sorbitol esters, sorbitan, sorbitan esters, isosorbide, isosorbide diesters and carboxylic acids, where the carboxylic acids themselves and the carboxylic acids on which the acid components of the esters mentioned are based correspond to the formula RCOOH in which R has the meaning given for formula (I), and the hydroxyl value of the mixture of the one or more compounds of the formula (I) and the one or more compounds selected from the group consisting of sorbitol, sorbitol esters, sorbitan, sorbitan esters, isosorbide, isosorbide diesters and carboxylic acids is smaller than or equal to 320, preferably smaller than or equal to 285, particularly preferably smaller than or equal to 245 and especially preferably smaller than or equal to 225.

13 . The composition as claimed in one or more of claims 1 to 12 , which comprises the one or more compounds of component a) in amounts of from 10.0 to 90.0% by weight, preferably in amounts of from 20.0 to 80.0% by weight, particularly preferably in amounts of from 30.0 to 70.0% by weight and especially preferably in amounts of from 40.0 to 60.0% by weight and the one or more substances of component b) in amounts of from 10.0 to 90.0% by weight, preferably in amounts of from 20.0 to 80.0% by weight, particularly preferably in amounts of from 30.0 to 70.0% by weight and especially preferably in amounts of from 40.0 to 60.0% by weight, in each case based on the total weight of the composition.

14 . The composition as claimed in one or more of claims 1 to 12 , wherein it is a cosmetic, dermatological or pharmaceutical composition, a crop protection formulation or a washing and cleaning composition.

15 . The composition as claimed in claim 14 , which comprises the one or more compounds of component a) in amounts of from 0.01 to 10.0% by weight, preferably in amounts of from 0.1 to 5.0% by weight, particularly preferably in amounts of from 0.2 to 3.0% by weight and especially preferably in amounts of from 0.5 to 2.0% by weight and the one or more substances of component b) in amounts of from 0.01 to 10.0% by weight, preferably in amounts of from 0.1 to 5.0% by weight, particularly preferably in amounts of from 0.2 to 3.0% by weight and especially preferably in amounts of from 0.5 to 2.0% by weight, in each case based on the total weight of the composition.

16 . The composition as claimed in claim 14 or 15 , wherein it is formulated on an aqueous or aqueous-alcoholic basis or is present as a solution, emulsion or dispersion and is preferably present as an emulsion.

17 . The composition as claimed in one or more of claims 14 to 16 , wherein it has a pH of from 2 to 11, preferably from 4.5 to 8.5 and particularly preferably from 5.5 to 8.

18 . The use of one or more compounds of the formula (I) as claimed in claim 1 and one or more aliphatic vicin

Assignees

• Pilz Maurice Frederic
• Klug Peter
• Scherl Franz-Xaver
• Grohmann Joerg
• Clariant Int Ltd

Inventors

• Pilz Maurice Frederic
• Klug Peter
• Scherl Franz-Xaver
• Grohmann Joerg

Classifications

• A01N43/90 Primary

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• A01N31/02

  Acyclic compounds · CPC title